Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines
摘要:
Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.
Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds
作者:Nikolai Yu. Kuznetsov、Rabdan M. Tikhov、Tatiana V. Strelkova、Yuri N. Bubnov
DOI:10.1021/acs.orglett.8b01317
日期:2018.6.15
Triallylborane–amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman’s imine was achieved with triallylborane–methylamine adduct.
Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolines
作者:Susan K. Armstrong、Stuart Warren、Eric W. Collington、Alan Naylor
DOI:10.1016/s0040-4039(00)79895-9
日期:1991.8
Allylic diphenylphosphine oxides (7) undergo stereoselective 1,3-dipolarcycloadditions with nitrile oxides to give Δ2-isoxazolines (8). These may be reduced, also stereoselectively, to δ-amino-β-hydroxyalkyldiphenylphosphine oxides (9). Stereospecific Wittig-Horner type elimination of Ph2PO2− from amino alcohols (9) gives homoallylic amines (10) with controlled double bond geometry.
烯丙基二苯基膦氧化物(7)经历立体选择性1,3-偶极环加成腈氧化物,得到Δ 2个-isoxazolines(8)。这些也可以立体选择性地还原为δ-氨基-β-羟烷基二苯基膦氧化物(9)。博士的立体有择的Wittig-霍纳型消除2 PO 2 -从氨基醇(9)给出高烯丙基胺(10)具有受控的双键的几何形状。
Armstrong, Susan K.; Collington, Eric W.; Knight, Julian G., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1433 - 1448
作者:Armstrong, Susan K.、Collington, Eric W.、Knight, Julian G.、Naylor, Alan、Warren, Stuart